N-(1,3-Dimethylbutyl)-N

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OECD SIDS N-(1,3-DIMETHYLBUTYL)-N´-PHENYL-1,4-PHENYLENEDIAMINE Kretzschmar and Neyen (1992) report that 6PPD is stable for at least 4 weeks in aqueous solutions at pH 2 in the cold, but will be degraded at neutral or basic pH within a few hours. Degradation of 6PPD in buffered aerobic solution and environmental water was examined in a study similar to OECD TG 111 (Bayer Industry Services 2003). 6PPD degradation in aerobic solutions is dependent on the temperature and on heavy metals. In buffered aerobic solution at 50 °C the half life of 6PPD is 5 h, which is increased to about 14 hat 26 °C. To simulate environmental conditions, 6PPD was dissolved in algae nutrient medium containing traces of ions of heavy metals such as Mn, Co, Cu, Mo, and Zn. Compared to buffered aerobic solution, in algae medium the half life period was significantly decreased to 8 h at 26 °C. 4-Hydroxydiphenylamine was identified as the major aromatic intermediate of 6PPD degradation under all conditions (Bayer Industry Services 2003)., From the time course of 4-hydroxydiphenylamine formation and degradation at 50 °C (Bayer Industry Services 2003), it is apparent that 4-hydroxydiphenylamine is not stable in aerobic media. Reports on stability of 6PPD and its analogues in water, are compiled in Table 4. 12 UNEP PUBLICATIONS
OECD SIDS N-(1,3-DIMETHYLBUTYL)-N´-PHENYL-1,4-PHENYLENEDIAMINE Table 4 Stability of 6PPD in water (IUCLID 3.1.2) Parameter Method Result Source Stability of 4-ADPA in water Stability of 4-ADPA in water Stability of IPPD in water Stability of 6PPD in water Stability of 6PPD in water Stability of 6PPD in water Degradation of 6PPD in pure and environmental water Aqueous test solutions under aerobic or anaerobic conditions, similar to OECD TG 111 OECD TG 111 Deionized water under aerobic conditions 4-ADPA abiotic degradation dependent on oxygen, heavy metals, and light. Estimated half lives at 50 °C: destilled water, anaerobic, darkness > 50 h; destilled water, aerobic, darkness 26 h; destilled water, aerobic, light 22 h; nutrient medium containing traces of heavy metals such as Mn, Co, Cu, Mo, and Zn, aerobic, light 7 h. 4-Hydroxydiphenylamine identified as degradation intermediate 4-ADPA half lives: 80 h at pH 4 57 h at pH 7 5 h at pH 9 IPPD degraded 99 % within 24 h N-Phenylbenzoquinone imine and 4- Hydroxydiphenylamine identified as degradation intermediates Bayer AG 2002a Bayer AG 2002b Monsanto 1992 Aerated water 6PPD half life less than 1 d Monsanto 1979a sterile and deionized water/sterile Mississippi river water. Aqueous solutions Aqueous test solutions under aerobic conditions, test design similar to OECD TG 111 6PPD half lives were 6.8 h in sterile and deionized water, and 3.9 h in sterile Mississippi river water containing traces of heavy metals 6PPD stable for weeks at pH 2 in the cold, but degraded within a few hours at neutral or basic pH In buffered aerobic solution at 50 °C the half life of 6PPD is about 5 h, at 26 °C it is about 14 h. In the presence of traces of heavy metals such as Mn, Co, Cu, Mo, and Zn, the half life decreased significantly. 4-Hydroxydiphenylamine was the major aromatic intermediate of 6PPD degradation Monsanto 1981 Kretzschmar and Neyen 1992 Bayer Industry Services 2003 2.2.4 Transport between Environmental Compartments According to the Mackay Fugacity Model Level I, the main target compartment for 6PPD is soil (95 %), followed by water (2 %) and sediment (2 %, Table 5, Bayer AG 2003b). However, due to rapid degradation (cf Chapters 2.2.3 and 2.2.5), the level 1 fugacity modelling has to be applied with caution. The degradation product of 6PPD and its analogues, 4-hydroxydiphenylamine is more soluble in water (water solubility 170 mg/l, log Kow = 2.46,) than 6PPD (EPA 2004). It is also neither stable in the atmosphere (t ½air = approximately 1 h) (EPA 2004) nor in aquatic media (cf Chapter 2.2.3). UNEP PUBLICATIONS 13
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N-(1,3-Dimethylbutyl)-N

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